Points of Views

This sets place after the ending of the episode "Family Remains" in season four. It's the moment after Dean has told Sam that not only did he torture souls in hell, but he actually liked it.
It's written so that the story jumps between the two brothers, told from their different perspectives.

. . .

[SAM]
Sam didn't know what to make of things. Everything he had believed in felt distorted in a way that was no longer recognizable.
Dean, his Dean, his older and only brother.
His hero.
How could he ever begin to grasp what he had just said to him?
All their life Dean had always acted tough, but no matter what, Sam had never questioned his brother's good heart or judgement. That was up until now.
Now he wasn't so sure any more, and that lack of blind faith in Dean made him angry. Sure, there had been times when they had fought each other, lied and hurt one another in near to unforgiving measures. But this feeling was new.
Dean didn't look back at him as Sam stared at his face, almost trying to make the words he had just spoken go back into his mouth, never to be uttered.
He had enjoyed it. He had taken pleasure in torturing other souls, like the way his had been for 30 years, down in the pit. Now Sam finally knew the true reason to why Dean had been acting weird after telling him, what he believed to be what happened in hell. This, however, had been left out that first time and now he wished that Dean would take it back, tell him it was all a joke. What a tasteless joke it would have been, but still, so much better than the option.
At first, Sam tried to make sense of it. He hadn't been to hell himself, so even if he would be told what it was like, he couldn't fully understand. Hadn't he done some bad decisions in life? He had demon blood in him, for pity's sake, in no way did he have an untainted soul. All those times with Ruby, who was a full blooded demon, no matter what his intentions were, that couldn't be ignored. Still, there was this feeling that he couldn't shake.
Disappointment.

[DEAN]
"How..." Sam started, but fell silent again. It had sounded more like a whimper than a word, and made Dean turn his eyes to his younger brother.
Sam, his Sammy. He never wanted to tell him, but the void inside him growing larger every second he didn't, pushed him to blurt it all out. It hurt him to confess it, but the thing that hurt him the most was the look in Sam's eyes. He had known him his entire life and if there was one thing he knew, it was that Sam never could lie with his eyes. What he saw looking back at him was so powerful it almost made him choke when he started to talk again.
"Sam, I wish I could tell you there was a way to explain it, but there isn't. I didn't know what it would be like down there when I sold my soul."
"Yet you didn't hesitate, did you?" Sam shouted, and the deep tone of his anger made Dean flinch. Or was it sadness? He couldn't say, but he felt the words like a drum inside his heart.

[SAM]
Sam sighed before he continued: "Dean, I don't know, I mean..." How could he find the words when he wasn't even sure what he wanted to say.
"What you did, for me, we can't change that. I can't undo it, but there is nothing I wouldn't do to be able to."
Dean turned his attention to something in the distant, maybe to hide frustration, maybe because looking at Sam was too painful.
"I never asked to be saved and if I'd known what would happen to you, I sure as hell wouldn't have wanted you to. I'm not looking for blame here, I'm just saying".
That last line was a lie and he knew it. Maybe Dean knew it too. He looked at him to see if he had reacted, but Dean just kept staring at nothing. Sam blamed Dean. He didn't want to, he couldn't help it, he just did. It's not that he wouldn't sacrifice himself for his brother, it was just that he felt guilty over Dean doing so.
Then there was the fact that Sam had felt abandoned by his brother, an irony he saw so clear.

[DEAN]
He couldn't turn his face back to Sam's, couldn't let him see that he was struggling not to cry. It wasn't that he was too proud to, Sam had seen him vulnerable many times before. He just didn't want Sam to see that he knew he was lying and that it made him so sad he could hardly breathe.
"I know I was selfish Sammy, I just wish you wouldn't judge me for it. I'm not blind you know, it's obvious that it's eating you."
"Damn straight it's eating me Dean!" Sam said as he walked over to Dean, forcing him to look at him.
"I'm scared and I can't help but thinking about what you did. It terrifies me, because if you could do such a thing, what can you expect from me?"
"What do you mean by that?" Dean asked, but he already knew what Sam was going to say.
"Think about it Dean, you are one hundred percent human, yet you did those things. You did them, and you liked it."
Those words hit Dean straight in the chest and he started yelling back: "You don't know what it was like..."
"No, I don't!" Sam screamed and with that large tears started to roll down his face.
"I don't know Dean, I don't and I'm trying to understand but the truth is I am so scared. I'm scared of what I will do, if you did those things. What will I do? Huh?! Just think about it." Sam hung his head and started to shiver. It looked like his face was leaking as tears fell straight down into the dirt.

Dean put a hand on Sam's right shoulder, but he shook it off. He grabbed him by both and Sam looked up, almost throwing himself in Dean's embrace.
They just stood there, Sam shaking in his brother's arms and Dean's heart was beating so hard it felt like it would explode. He couldn't stand Sam being hurt like this, and even worse, by him.